In addition to jar changes, a plugin update can also make data or configuration changes. First save the old version and its data for rollback.
Step by step
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Check Java, Minecraft and dependency requirements in the plugin's release notes. If the data format changes, re-read the instruction.
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Shut down the server properly. Backup the old jar file, plugin directory and external database if necessary.
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First, open the test copy with the new jar. Control automatic configuration transformation, permissions and important processes used by the player.
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In live, replace the old jar with a new one and restart. If there is an opening error or data mismatch, go back to the old jar and data backup taken together.
Keep in mind
Updating several independent plugins at the same time makes it difficult to trace the source of the problem.